Water → 5-Methoxy 3-(1,2,3,6-tetrahydro-4-pyridinyl)1H indole

HRID 2357499Notes

Reaction equation

HRID 2357499 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2.Cl.[NH:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1.O>CO>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[C:18]1[CH2:19][CH2:20][NH:15][CH2:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 138725-MethoxyindoleHCID 14797Potassium HydroxideHCID 30848514-Piperidone hydrochloride

Product 1

HCID 1080295-Methoxy 3-(1,2,3,6-tetrahydro-4-pyridinyl)1H indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

KOH (8.44 g, 150 mmole), 5-methoxyindole (5.0 g, 34 mmole) and piperidine-4-one hydrochloride (10.53 g, 88.3 mmole) were suspended in methanol (50 ml) and heated for 8 hours at 65° C. under argon. Water (50 ml) was added dropwise at RT to the mixture over a period of 40 minutes. The solid thereby formed was filtered off, washed with water (3×20 ml) and recrystallised from methanol (20 ml). 5-methoxy-3-(1,2,3,6-tetrahydropyridine-4-yl)-1H-indole was obtained in a yield of 4.66 g (75%) as a yellow solid with an m.p. of 173°-175° C.

Workup

  1. customThe solid thereby formed
  2. filtrationwas filtered off
  3. washwashed with water (3×20 ml)
  4. customrecrystallised from methanol (20 ml)

Sources & evidence

ORD record
ord-8395e0b8258345898e788cdde5008f18
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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